Substituent effect on the electronic properties of pyrazino[2,3-g] quinoxaline molecules

Tam, Teck Lip Dexter; Zhou, Feng; Li, Hairong; Pang, Jane Chieh Yu; Lam, Yeng Ming; Mhaisalkar, Subodh; Su, Haibin; Grimsdale, Andrew C.

doi:10.1039/c1jm12347e

Cited by 12 publications

(12 citation statements)

References 28 publications

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“…3. The calculated values for PQs have been previously reported by us, 25 whereas the values for the TQs were derived in the current work.…”

Section: Polymer Synthesesmentioning

confidence: 90%

“…14,26,27 pTQ2F and pPQ2F also showed a slightly lower bandgap than pTQ1F and pPQ1F respectively due to the higher conjugation of the bithienyls as compared to the biphenyls. 25 The different substituents on TQ did not cause any significant change in the energy levels for the TQ polymers. However, a more pronounced effect on the absorption spectra was easily seen from the less obvious valley at $600 nm for pTQ2F as compared to pTQ1F.…”

Section: Photophysical and Electrochemical Propertiesmentioning

confidence: 93%

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From benzobisthiadiazole, thiadiazoloquinoxaline to pyrazinoquinoxaline based polymers: effects of aromatic substituents on the performance of organic photovoltaics

Tam

Salim

et al. 2012

J. Mater. Chem.

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“…3. The calculated values for PQs have been previously reported by us, 25 whereas the values for the TQs were derived in the current work.…”

Section: Polymer Synthesesmentioning

confidence: 90%

Section: Photophysical and Electrochemical Propertiesmentioning

confidence: 93%

From benzobisthiadiazole, thiadiazoloquinoxaline to pyrazinoquinoxaline based polymers: effects of aromatic substituents on the performance of organic photovoltaics

Tam

Salim

et al. 2012

J. Mater. Chem.

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“…For example, our earlier studies show that by replacing the bis(biphenyl) group in compound 6 with the bis(bithienyl) group with a higher quinoid character to reduce the LUMO, the optical gap of TQ-X0 was reduced from to 2.26 eV to 1.99 eV as in TQ0, 34 and TQ-X2 from 1.70 eV to 1.65 eV as in TQ2. 34 The same methodology applies to PQs as we reported earlier, 42 however, as will be discussed later, care must be taken to avoid losing molecular stability.…”

Section: Electrochemical Propertiesmentioning

confidence: 98%

Comparative studies on the electrochemical and optical properties of representative benzo[1,2-c;4,5-c′]bis[1,2,5]thiadiazole, [1,2,5]-thiadiazolo[3,4-g]quinoxaline and pyrazino[2,3-g]quinoxaline derivatives

Zhou

Tam

et al. 2013

J. Mater. Chem. C

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“…[30] Grimsdale and co-workers further extended the conjugation and introduced substituents at the quinoidal positions to study the electronic properties of the pyrazino[2,3-g]quinoxaline derivatives. [31] A water-soluble pyrazino [2,3-g]quinoxaline based photosensitizer reported by A new pyrazino[2,3-g]quinoxaline carbazole derivative with branched alkyl peripheral chains PQC-12b with a donor-acceptor-donor nonplanar architecture is reported. PQC-12b exhibits high molar extinction coefficients, low bandgap, bright emission behavior in solution and solid-state, along with positive solvatochromism.…”

mentioning

confidence: 99%

A New Class of Solution Processable Pyrazino[2,3‐g]quinoxaline Carbazole Derivative Based on D–A–D Architecture for Achieving High EQE in Yellow and White OLEDs

Vishwakarma

Nagar

Lhouvum

et al. 2022

Advanced Optical Materials

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level. Carbazole-containing polymers were used as organic light-emitting diodes, [1][2][3] photovoltaic cells, [4,5] and thin-film transistors. [6,7] They have also found application in electrochromic devices as they can form relatively stable cations on the application of voltage. [8,9] Carbazole-based compounds also found application in the synthesis of several thermally activated delayed fluorescence (TADF) materials, which are capable of enhancing the emission efficiency of present-day organic light-emitting diodes (OLEDs) by harvesting the excitons in a triplet state. [10,11] However, the realization of such beneficial materials requires the proper combination of carbazoles with suitable acceptor units with a twisted structure with a reduced energy gap between the singlet and triplet states. Carbazoles are also utilized as donor units in donor-acceptor (D-A) compounds with a high potential for synthetic tunability, ambipolar charge transport, and light-emitting materials with high emission efficiency. [12][13][14][15] A wide variety of carbazole derivatives are used in fluorescent and phosphorescent OLEDs due to their suitable energy levels, good charge transport behavior, and high triplet energies as host materials. [16][17][18][19][20][21] Being an inexpensive, stable starting material with the ease of functionalization by N-alkylation and core modification, carbazole provides enormous opportunities for structural modifications to realize functional materials. [22] Quinoxaline derivatives also have been used in organic electronic devices like organic solar cells, [23,24] OLEDs, [25] and organic field effect transistors (OFETs). [26] They have also found application in the construction of supramolecular self-assembling materials, [27] sensors, [28] and also as acceptor units in the building of D-A systems with low energy gaps. [29] Pei and co-workers developed tetrasubstituted pyrazino[2,3g]quinoxaline derivatives with thiophene and phenyl rings, which leads to varying extent of conjugation to achieve highefficiency active waveguide fibers. [30] Grimsdale and co-workers further extended the conjugation and introduced substituents at the quinoidal positions to study the electronic properties of the pyrazino[2,3-g]quinoxaline derivatives. [31] A water-soluble pyrazino [2,3-g]quinoxaline based photosensitizer reported by A new pyrazino[2,3-g]quinoxaline carbazole derivative with branched alkyl peripheral chains PQC-12b with a donor-acceptor-donor nonplanar architecture is reported. PQC-12b exhibits high molar extinction coefficients, low bandgap, bright emission behavior in solution and solid-state, along with positive solvatochromism. PQC-12b is used in organic light-emitting diodes (OLEDs) either as sole emissive material or as a guest in different host materials. Amongst these different host-guest OLEDs, CBP-based device with the optimized concentration of PQC-12b shows maximum values for power efficacy (PE max ) of 14.1 lm W −1 , current efficacy of 26.8 cd A −1 , external quantum efficiency (EQE max ) of ...

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Substituent effect on the electronic properties of pyrazino[2,3-g] quinoxaline molecules

Cited by 12 publications

References 28 publications

From benzobisthiadiazole, thiadiazoloquinoxaline to pyrazinoquinoxaline based polymers: effects of aromatic substituents on the performance of organic photovoltaics

From benzobisthiadiazole, thiadiazoloquinoxaline to pyrazinoquinoxaline based polymers: effects of aromatic substituents on the performance of organic photovoltaics

Comparative studies on the electrochemical and optical properties of representative benzo[1,2-c;4,5-c′]bis[1,2,5]thiadiazole, [1,2,5]-thiadiazolo[3,4-g]quinoxaline and pyrazino[2,3-g]quinoxaline derivatives

A New Class of Solution Processable Pyrazino[2,3‐g]quinoxaline Carbazole Derivative Based on D–A–D Architecture for Achieving High EQE in Yellow and White OLEDs

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